


Diamonds and Daddies

by Dadolorian



Series: SugarDaddy!Whiskey AU [1]
Category: Kingsman (Movies)
Genre: Aftercare, Daddy Kink, Dirty Talk, Explicit Sexual Content, F/M, Fingering, Oral Sex, Smut, Spanking, Sugar Daddy, Vaginal Sex, cheating mentioned, chocking, consent talk, dd/lg, face riding, healthy communnication, posessive language, protection discussion, reaffirming consent, respect women juice
Language: English
Status: In-Progress
Published: 2020-12-12
Updated: 2021-01-03
Packaged: 2021-03-11 00:41:02
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 14,452
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28036323
Author URL: https://archiveofourown.org/users/Dadolorian/pseuds/Dadolorian
Summary: Whiskey tries Tinder, and when that doesn’t work discovers a Sugar Baby app that has him most intrigued.
Relationships: Jack | Whiskey (Kingsman)/Reader
Series: SugarDaddy!Whiskey AU [1]
Series URL: https://archiveofourown.org/series/2100495
Comments: 25
Kudos: 138





	1. Rules and Regulations

**Author's Note:**

> I've tried to make this reader character a little more inclusive, my other 3 major x reader fics have readers with specific body types or descriptions (Disabled, small/skinny or curvy) , this one apart from reader being a Cis female i have made the effort of putting as little physical description into her features as possible.  
> Shes describes as being gorgeous and glamorous (because she takes up Sugar Baby gigs, gotta look glammed up for those rich Daddies ), but other than being glammed up and what she wears there is little to no physical description about her. 
> 
> Reader’s main job is a sugar baby and i don’t want any shitty comments about that thanks. 
> 
> This fic isn’t for everyone, please make sure you read the warnings.  
> Thank you @oloreaa and @ahimavirgin on tumblr for being my Beta readers!

Jack was not the most technologically savvy man in the world. 

  
Eggsy,  _ the little shit _ , often decided to remind the senior Statesman agent of the hilarious cluenessless he displayed when their target,  _ Clara _ rejected him with a tinder joke.    
  
“For an old man who thinks he’s god’s gift to women you would think you knew what fucking tinder was ay Bruv?” he had laughed. ‘ _ “What’s ‘Tender?’”’  _ He had mocked.   
  
It was all jokes among friends until the _ little shit  _ encouraged him to try it out one evening at a bar, surrounded by his peers. He couldn’t turn it down without some friendly jeering sent his way. 

  
Ginger had shown him how to download the app.    
  
And, while his endeavors in exploring the app and what it had to offer were fruitless, it had led him down a rabbit hole of related apps.    
So when an app for Sugar babies and Daddies showed up in his recommendation, Jack found himself utterly _ intrigued _ . 

He had scrolled through the app for a while, not really finding anyone who’s appearance and profile fit his desires until he landed on  _ you. _ _  
_ He was smitten _ immediately _ , browsing through your small gallery, staring at each photo longingly. Burning your image into his memory lest he never see such a  _ goddess _ again.  _ Everything _ about you got his heart racing, your hair, eyes, lips, smile, body, skin, he could get lost in just how perfectly everything about you fit together to create such a beauty.    
You knew how to dress to best accentuate your features, his personal favorites were the white lacy numbers that made you look sexy as sin, but oh so innocent at the same time, the big doe eyes you gave the camera weren’t helping either.    
Oh how he could imagine you batting those pretty eyelashes up at him with your innocent little pout. Pretending to be an  _ innocent little thing  _ before he took you to bed and made you  _ scream _ for him. His pants were tightening at just the thought.    
There was no way,  _ no way _ , he would squander an opportunity to have _ you _ in his life.    
  
He read the brief profile, it listed your username (Fake obviously), age and what you were looking for:   
_ “A big strong Daddy to take good care of me.” _ _  
_ Fuck...He could do  _ just that _ .   
  
He was quickly messaging you, and you were pleasantly surprised when your phone notified you of his messages that evening, more than used to messages that were more of a demanding and demeaning nature or more objectifying. His messages were genuine, and even sweet.    
  
**Jack🤠:** I hope this aint too forward Darlin but i just need to tell you you are the most gorgeous woman i have ever seen. 😍

**Jack🤠:** Any man would be lucky to have you on his arm that for sure. 

**Jack🤠:** You are absolutely stunning, I am completely breathless. ♥♥

**Jack🤠:** You are just as ♥♥pretty♥♥ as a peach. 

**Jack🤠:** I hope my messages don’t bother you i simply can’t help myself, i think i’m smitten. ♥

**Jack🤠:** What would it take for us to get to know one another?? 

**Jack🤠:** I think we would go together like peas and carrots. ♥♥   
  


  
From there the two of you were chatting at every available opportunity, Jack laying the charm on  _ thick _ , and in less than a week the two of you had hit it off over text and arranged a date to make things official and set terms.   
The  _ sweetheart _ had even sent along a hefty in-app tip so you could spoil yourself and get glammed up for the night, much to your utter delight.    
His charm had won you over pretty quickly, and you were just as excited for your date as he was. 

\-------------------------------------------------------------------------------------------------------------------------------------------

  
  


When date night finally rolled around Jack had excitedly left work early so he could get himself ready. Not wanting to wear his office attire of the blazer and jeans combo he opted for something a little more …  _ dapper, _ so he stood in his underwear as he went through his entire collection of suits he had collected for Statesman gala’s over the years, scrutinizing over each choice wondering hopelessly if you would like each one. Trying them on and checking himself out in the mirror and trying a few pick up lines before cursing when he decided his latest choice just wasn’t  _ good enough _ then hanging it back up and moving onto the next.   
  
“Howdy, Darlin,” he smiled into the mirror wearing a plain black velvet tux, scowling when he realized he looked like he was going to a movie premier rather than a  _ date _ .    
  
He followed it up with an all black suit and shirt combo, trying another line of “Hey there gorgeous,” into the mirror before scoffing again. “Look like I'm attending a god damn  _ funeral _ ,” he muttered, stripping out of yet another suit. 

  
Despite the extra time he had given himself, he had spent far too long in front of his mirror agonizing over his choice of clothes for the evening he had  _ almost _ made himself late.    
  
He barely had enough time to shower after grabbing the final suit he had inspected, running so late that he had left home without even shaving, hoping to hell you liked the slight scruff he was sporting. 

* * *

  
  


_ Somehow  _ he managed to arrive at the restaurant before you, egging his driver to go just a  _ little  _ faster in order to make it in time. Possibly breaking a few speed restrictions here and there, but statesman drivers were trained to get their agents away from pursuing enemies, getting to a date in time would be a  _ piece of cake.  _

Once he was in front of the restaurant and confirmed you were still on your way he smoothed his suit and hair into place before entering the building.    
Once the hostess had shown him to his table he found himself feeling...nervous. A feeling he hadn’t felt in a long time when it came to women.   
He was usually so brash, when it came to charming a woman...But a  _ date? _ … A  _ real  _ one? That had been quite a while.He hadn’t been on one of those since he was dating his wife…   
  
He shook his head, banishing those thoughts for the evening, he didn’t want to feel any guilt for what he was about to do.   
He still loved her, of course, but she was his past, living in it would only give him more heartache. If he focused too much on the past, he’d never be able to find happiness like that again. 

He _ ached _ for companionship, for the attention of a beautiful woman, too tired of the random hook ups and never seeing the same woman twice, the usual dating scene didn’t suit him, he was too ‘old fashioned’ and scarred by his lost love to put himself out there like that, and after what happened...he needed...control. If he was in control, then he wouldn't need to lose anyone again.    
  
He was able to drag himself out of his mental anguish as the Hostess came into view once more, followed by his goddess.    
His breath caught in his throat at the first glance of you, distracting him from whatever he had been thinking about, awestruck.   
  
Something he had loved in your photos was that you really knew how to dress to show off your best features, you wore a short white cocktail dress that hung over your shoulders, the lace overlay hugged your skin and covered your arms, matching white heels made your legs look shapely and endless. Your hair, makeup and nails were made to perfection, he thought you looked glamorous, like a moviestar.    
  
Quickly getting up on his feet to greet you Jack gave you his best, charming smile.    
  
“Howdy there, Darlin,” he greeted in his southern drawl as the hostess left you two alone to read through your menus. “Seem’s I was not wrong, you truly are the most gorgeous creature I have ever had the pleasure of meeting,” he continued, gently taking your hand in his, placing a kiss a top of it.    
  
You smiled up at him, a faint blush appearing on your cheeks to his delight. “It’s a pleasure to meet you too,  _ Jack _ ,” you said, and his heart skipped a beat yet again at your voice.  _ Angelic.  _ _  
  
_

He had seen your photos , but he didn’t post any of his to his profile, he claimed he did not want anyone from his personal life to discover him on the app, which was fair enough, he had sent you a few photos through private messages, and at the time you were skeptical they were...current photos. Many of your past dates had a habit of showing you photos that were more than a decade old, failing to tell you they were now...past their prime so to say.    
You were grateful he had not done that, that he truly was as handsome as the photo’s you had received. It flattered you that a man this handsome had been the one flirting and charming his way into your heart for the past few days. 

  
“The pleasures all mine, Darlin,  _ truly _ ,” he said, motioning for you to sit down.   
“Let’s decide what we want before we get to anything else, alright Baby?” he suggested, joining you and picking up the menu.    
  
You nodded picking up your own menu, having a quick read of it.    
  
Ever the country boy at heart Jack went with the classic steak meal, along with a bottle of wine for you to share, he was tempted to order his namesake, Whiskey, but he wanted something less of an acquired taste for the two of you to drink together.   
  
When you said you wanted to order the salad,  _ the cheapest meal on the menu _ he noted, he almost shook his head.    
He had half a mind to ask you what you  _ really _ wanted, but that felt a little...condescending.    
  
“If that’s what you want, Baby, so be it,” he said. “But I hope I can convince you to go all out for dessert,” he chuckled.    
  
Once your order was taken Jack carefully placed one arm over the back of the booth, and his other hand on your knee, watching carefully for any signs of discomfort, but you bit your lip and smiled shyly at him.    
  
“Now Baby, I’m afraid you’re going to have to take the reins tonight,” he started, rubbing gentle circles into your skin with his thumb. “This is my first date in...quite a while, and i’ve never entertained the thought of having a Sugar baby until this week, I feel a little...  _ out of my element  _ here.”    
  
“That’s okay, Daddy, “ you purred, snuggling up to his side and sending a small shiver down his spine. “I can answer any questions you may have, we can get to know one another, and if we both want to, we can discuss our terms if we want to make this more than a one time thing.”    
  
“Well I can already tell you, i’m _ not _ after a one time thing with you...I’d be a  _ fool  _ to turn you away from anything more.”    
  
“I’m really happy to hear that,” you batted your eyelashes up at him, smiling. “I don’t want a one time thing either. I just want a Daddy who can take good care of me.”    
  
“I’d be more than happy to do just that, Darlin,” he said , lifting his hand to gently cup your face, his thumb stroking your bottom lip teasingly.    
  
He didn’t miss the way your eyes flicked down to his own lips in expectation.    
  
“You said something about ‘terms’...mind explaining that to me Sugar?” he asked, dropping his gentle grasp on your face much to your disappointment. His hand however was quickly back on your knee without missing a beat.    
  
“Term’s are what our hard rules are...Our expectations for a relationship and limits,” you explained. “I’m already aware of what my terms are… I want exclusivity, which means no other partners for either of us, a livable allowance, an established safeword which must be respected, and the rest is up for negotiation.”   
  
He nodded in agreement. “That sounds more than fair Darlin, I think I am in  _ full  _ agreement with you.”    
  
You were about to question him on if he truly understood what that meant when a waiter came back to deliver your choice of wine. Ever the gentleman he poured each of you a glass.    
  
With a glass in hand each you smiled at each other.    
  
“I agree to your terms Darlin, and anything else I think is up for us to decide together or negotiate. Deal?” He held his glass up, inviting you to clink glasses and seal the deal. 

“You agree to it all? The exclusivity?” you questioned, a little skeptical.    
  
“That's so hard to believe sugar?” he asked, more amused than offended by the question.    
  
“Well, you’ve proven to me in our texts you’re a real charmer Daddy, it wouldn’t surprise me at all if you flirted with any pretty thing that caught your eye.”    
  
He hummed in thought, you were pretty spot on.    
“I’ll admit Darlin, I am a bit of a flirt…” he confessed. “But I ain’t a cheater, I may throw on the charm to a pretty lady but I would never disrespect you and make moves on another woman after promising to be exclusive to you,” he placed his glass down and squeezed your leg gently to affirm his point.   
“I ain't a hypocrite, I know I’d be mighty upset if I saw you flirting with another man...I  _ want _ exclusivity with you, and I’m willing to tone down my charm with other women if that makes you  _ happy _ ...All I want is a pretty little thing like you to take care of and make happy. If you’re happy then _ I'm _ happy.”    
  


Your skeptical look was slowly replaced with a look of delighted surprise. “Then it’s a deal Daddy,” you smiled excitedly, raising your own glass and the two of you toasted to your future together. 

With  _ business _ out of the way, Jack wanted to start getting to know you more  _ personally _ throughout the rest of the date.    
You told him your real name, and that you were currently a bartender, but were only working while you had been searching for a full time Daddy. He was not at all disappointed to find out that you intended to quit now that he agreed to your terms and would be giving you an allowance. You told him of your past Sugar Baby experience, without breaking any of your past Daddies trust by naming them. You had been with a few Daddies in the past but never able to keep the relationship going due to lack of interest on their part, you were either tossed aside for the next flavor of the month or found yourself with Daddies with commitment issues. You even told him of the horror story of the Daddy who kept you for close to a year, only to find out he was married and you were one of many Baby’s he was seeing.   
  
He told her of his job...not the entire truth, just his public image as a C.E.O. of a Bourbon whiskey distillery. What that job entails, the Whiskey making process, the type of people and places he needs to see.    
  
As your meals arrived he listened carefully as you spoke about your life, hobbies and interests. At your mention of your love for animals he promised to take you down to his ranch and let you meet each of his critters he had, and when you mentioned how you would love to travel more he promised to take you with him on a few business trips if the situation allowed it. 

* * *

The two of you laughed and flirted back and forth for what felt like hours, so lost in each other's company that neither of you paid attention to the time.    
As promised Jack had managed to convince you to treat yourself with the dessert, but only after promising to share it with you. He noticed you were a cautious spender, he wasn’t sure if it was a personality thing or a habit out of necessity, saving every penny while you were between Daddy’s with fat wallets, he hoped as you grew closer you would feel more comfortable indulging yourself… He did want to spoil his Baby, after all.   
  
When the time eventually came to leave, even after stalling with an after dinner coffee each Jack led you to his car where his driver waited for you both.    
  
“Darlin, this is your choice…” he said, cupping your face in his hands gently, stroking your cheek with this thumb. “You can either come back to my place...Or we can drop you home, you’re under no pressure tonight for  _ anything _ , all I wanted was to meet you and get to know you, my expectations for this evening have already been met.”    
  
You looked up at him, eyes sparkling with excitement. “I want to go home with my Daddy,” you purred.    
  
He growled in response, pulling you in for a deep kiss. His tongue teased your lower lip, asking for entrance, and when you gave it, he took control, cupping your jaw as his tongue met yours and your teeth, sweeping across them teasingly.    
He tasted like the coffee you had both shared, sweet and bitter at the same time and you loved the way he smelt like his subtle cologne, something with a light vanilla smell that didn’t overpower his natural scent, instead only complimented it.   
_ His thoughts seemed to mirror yours _ , for he found that he loved the floral scent of your perfume, again nothing too strong as to overpower your natural scent,  _ like faint lavender _ . Your arms looped around his neck in an attempt to deepen the kiss even further, which he allowed for only a brief moment before he broke the kiss, much to your disappointment. 

  
“Hop in then.” He opened the car door for you, resisting the urge to playfully smack your ass as you climbed in.   
“Back home,” he instructed the driver once he was sitting down next to you.    
  
He glanced over to you with a smile, before leaning over and securing your seatbelt for you, stealing a quick kiss as he did so. He rested his hand on your thigh posessively once you were all buckled up safely.   
For the drive back to his place he was rather quiet, his free hand on his chin in thought as he started out the window, the only indication that he remembered your presence was the gentle strokes of his hand on your thigh. 

You watch him from the corner of your eye as the New York lights streamed across his handsome face as you passed them.

It was not an uncomfortable silence, he was clearly lost in thought, but relaxed, there was no awkward tension in the air and you took the opportunity to take in just how handsome he really was.   
He was good looking, rich, charming, wanted to take care of you, and willing to commit to you and  _ only _ you...You felt like the luckiest girl in the world. 

When the car stopped, he hurried out to open the door for you, holding his hand out for you to take like the gentleman he was and flashing you another boyish smile. God, his  _ smile _ , you felt like a schoolgirl every time you saw that cheeky dimple of his, you could feel the heat that rose to your face and by his cocky expression, you knew _ he _ knew just what kind of effect he was having on you.    
  
You distracted yourself from him by looking up at the tall building you were parked in front of, it really didn’t surprise you that he lived in such a swanky apartment building with the amount of cash he seemed to be comfortable spending on you and his profession.   
You weren't familiar with the area, but you would harbor a guess on your location and imagined he had a balcony view of central park.

  
He nodded a greeting at the doorman as he led you inside, arm around you possessively , hand resting on your hip dangerously close to your ass but you didn’t complain, you more than enjoyed his attention.    
  
The lobby was all polished marble, cool colors, neat potted plants and antique furniture, you would have loved to admire the extravagance but you were pulled into the elevator with him rather quickly before you could enjoy the scenery of it all.    
  
He pushed the button to the penthouse suite without taking his hand from you, flashing you another smile when he caught you admiring him from the corner of your eye again.    
He chuckled when you looked away bashfully, teasingly rubbing your hip with his hand.

The elevator dinged open and he led you to his impressive doors, unlocking and holding one open for you.    
“After you, Darlin,’’ he hummed.   
  


His apartment didn’t fit in with the rest of the buildings theme, sure it was all high quality and extravagant... but there was no polished marble, antique chairs or neatly trimmed potted plants. You made your way out of the large entrance curiously, taking the time to admit it. It was more... rustic and warm than the lobby, with exposed brick walls and sturdy wooden furniture, armchairs made of soft, worn leather, a few rather tasteful decorations littered about the place, some antlers hanging from the wall. There was also a western movie poster framed, a drinks cart. It was like the country met the big city, and was so very  _ him.  _ _  
_ _  
_ “Take a seat Darlin,” he said motioning to the couch heading to the drinks cart. “Can I interest you in a drink?” he asked, fixing himself a glass of whiskey.    
You politely declined the offer, waiting for him to join you on the couch.    
  
Drink in hand he collapsed carefully on the couch next to you, inviting you to snuggle up to him silently by raising his free arm to you. You accepted the invitation quite happily and hooked your legs over his, resting your head on his shoulder.    
  
“Now that we’re  _ alone, _ baby,’’ he said, voice dropping a little lower as he gently stroked the exposed skin of your shoulder. “How bout you and I have a more  _ serious _ discussion about our rules?”    
  
You nodded eagerly. “Sound’s _ perfect _ Daddy,” you grinned, shivering slightly at the husky tone his voice took on.    
“Right, well Darlin,” he said, taking a sip of his Whiskey. “I have a few rules… number one is, you can  _ never _ go into my office without permission.”    
He waited until you nodded in agreement before he continued.   
“I _ mean _ it...this ain't one of those things where you’ll get a ‘punishment’, this ones a serious rule and I'll end our little agreement if I ever find out you’ve gone in there without my permission. You understand, Baby?” he asked, shifting to look into your eyes, maintaining fierce eye contact waiting on your answer.    
  
“Yes Daddy, I understand.”    
  
“Good,” he said, giving you a quick kiss as a  _ thank you _ and settling you back onto his shoulder. “My second rule… Is that your pleasure, punishments _ and  _ rewards, all belong to me… I’ll decide what's a punishment, what's a reward, and if or  _ when _ you get pleasure, including when we’re apart...If I find out you’ve broken the rules, you’ll be punished...That agreeable with you?”

You nodded again eagerly, pulse quickening in excitement at the implications. “Yes, that sounds good,” you agreed. 

“My third rule, I want you to deactivate your profile on the app...I’ll deactivate mine too. I’m taking care of you now, you don’t need any other Daddy except for me,” he growled into your ear, nibbling it possessively.   
  
You mewled, breathlessly agreeing to the rule as he moved to trail down your neck and across your chest, only stopping once he reached the material of your dress. 

“My fourth and final rule is I don't want to use a condom,” he said, watching your reaction carefully. You kept your face neutral, waiting for him to continue.    
“I’ll pay for whatever birth control option you want, and I’ll have the two of us tested before we get to that point, and as regularly as you want,” he continued. “But once we’re in the clear I want you without a barrier, I want to be able to fill you up.”    
  
“And if birth control should ever fail?” you asked trepidatiously.    
  
“If god forbids it fails, I  _ promise _ you we will handle that situation however  _ you _ want to. That's  _ your _ decision and I will  _ continue _ to take care of you.”

  
You searched his eyes for his resolve, they were staring back at you with a determination that made you believe him and trust him.

“No matter my decision?” you asked, wanting to be reaffirmed.    
  
“No matter your decision,” he confirmed, giving your shoulder a comforting squeeze and kissing your forehead.    
  
“Okay...but until we have both been tested and I have an IUD to replace my birth control pills,  _ you _ use a condom,” you said, raising your chin slightly in challenge.    
  
“Deal,” he said, giving you another kiss to seal the deal. 

“Apart from that, and your terms from earlier, I don't really have any more rules. You’ll be ‘punished’ for being a ‘brat’, and rewarded for being ‘good’, I'll take care of you in every sense of the word, and you’ll make yourself available to me at my request, within reason of course.”    
  
You nodded eagerly again, a giddy smile on your face, he was the  _ perfect _ one for you. 

“Do you have any more terms or rules  _ you  _ want to throw in?” he asked, making sure the two of you were both on the same page.    
  
“Well, apart from the obvious, use of a safe word that must be respected, good communication, and honesty...I don’t have any particular rules, so long as you make sure we’ve discussed any new things either of us want to bring into our arrangement beforehand,”   
  
“That’s all part of good communication, Hon',” he drawled before finishing off his small glass. 

“I have two things I want to make clear though...Taking care of me means more than giving me money, I've been with a couple of Daddies who forget that there's emotional needs too..I don't want to be ignored when I'm not giving you ‘sugar’.” You paused and he took the opportunity to gently kiss you again, he tasted like his whiskey, it was rich and smooth.    
  
“You weren’t with very good men then, Darlin… when I said I'll take care of you, in  _ every _ sense of the word, I  _ mean _ it. I  _ promise _ ” he said, giving you a soft quirk of his lips. His smile widened when you beamed back, overwhelmed with glee at just how damn perfect he seemed to be for you. 

“The second thing is for some reason we ever end our arrangement, I would like the allowance to continue long enough for me to be self-sufficient again,” you said, pleased and relieved when he nodded in agreement too.    
  
“Well now, do we need to get any of this in writing?” he asked jokingly.    
  
“There’s no official contract, however it would be good for us to write down everything we agreed to to make things easier.” 

He put his glass down and his now free hand made its way to your thigh, playing with the hem of your dress teasingly.    
  
“That's fair enough, how bout we get to that in the morning...and have a little fun now that business is all out of the way?” he asked, brushing his nose up against yours, teasing you by backing off when you moved forward to kiss him. He did it a few more times, backing off each time you went for a kiss.   
  


“Daddy,  _ please _ ,” you whined, pouting at him when he chuckled at you.    
  
“Please  _ wha _ t Darlin?”    
  
“Please don't tease me,” you pleaded, batting your eyes at him. 

He patted your thigh gleefully. “Those pretty little eyes won't always work on me, Darlin, but since this will be our first time together I intend to  _ spoil  _ you,” he purred, standing up and lifting you up with him, you wrapped your legs around his waist instinctively.    
“Is this alright with you, Baby?” he asked as he made his way over to the stairs.    
  
“More than alright, Daddy,” you huffed excitedly, impressed at the ease of which he seemed to pick you up with. He was surprisingly fit for a businessman.

  
“What’s your safe word?” he asked, refusing to move until you had both established it.    
  


“I prefer the traffic light system, Red is stop, yellow is pause, green is go,” you explained, running your fingers over the hair at the base of his neck.   
  
“Simple, easy to remember. I like it,” he grinned before kissing you roughly, nipping at your lower lip, only pausing to ascend the stairs, still carrying you.   
  
As soon as you reached the top his lips were back on yours, nibbling hard enough you had a feeling there would be marks later.    
  
He roughly swun the door open, too distracted by the kiss to even look where he was going, he knew his home well enough to lead you both over to the bed, dropping you onto his mattress with an ‘oof’.   
  
“Tonight, Baby, I want you to show me just how you like it, fuck yourself on me, show me just how you want to be taken,” he growled tossing his jacket and tie off to the side and began to unbutton his dress shirt.    
“How’s that sound?” he asked when he was shirtless, pleased at the way you were distracted by the show to even answer his question.    
  
He snapped his fingers to bring your attention away from his soft belly and strong arms.    
  
“Huh?”    
  
“I  _ asked, _ Darlin… if you like the sound of fucking yourself on me, and showing me just how you like it?” He bent over the mattress, planting one hand by your head and the other on your thigh, trapping you there and holding your gaze. “Well?”    
  
“That sounds real good, Daddy,” you nodded, squirming under his intense gaze, biting your lips.    
  
“Good,” he said, giving you another quick kiss and stood up, he started unbuckling his belt, loving the way your gaze drifted right back down. “Come on Baby, as much as i  _ love _ that dress you need to take it off before i  _ rip it off _ .”    
  
You swallowed and nodded, shimmying the dress up over your head, tossing it to the floor. The off the shoulder look of the dress didn’t really allow you to wear a bra, leaving you only in your heels and panties.    
  
“Fucking perfect” he growled, leaning back over to cup one of your breasts, rolling a nipple between his thumb and forefinger until it was a bud. You arched into his touch and he quickly latched his mouth onto the other one, showering each with his attention.    
He was not gentle, but he was careful not to actually hurt you as he squeezed and nipped at your skin, switching and not stopping until you were littered with faint love bites all over your chest.    
  
“There...Sporting Daddy’s marks _ real nice _ there Baby,” he said proudly, as he went to unbutton his pants. 

  
The rather impressive bulge was let free slapping against his belly, as he had apparently gone without his underwear for the evening.    
  
Your mouth watered at the sight, sitting up immediately, instantly begging to taste it.    
  
“Oh Daddy, please let me taste you, I want you in my mouth so bad. Let me suck your cock, Daddy,  _ please _ ,” you pleaded, batting your eyelashes up at him again and reaching out to take him in your hand, stroking him slowly from base to tip.    
  
He groaned loudly, head tipping back as he enjoyed the sensation of you squeezing him.    
  
“God, whatever you _ fucking want _ tonight baby, _ fuck _ , I wont say no to that,” he moaned, attempting to take off his pants fully without loosing your hand on him.    
  
Once he was completely naked, he pushed your hand away gently, making you whine and pout up at him.   
  
“Shhhh,  _ none _ of that baby,” he soothed, cupping your face to kiss you. “Let Daddy get comfy and then you’re free to play with his cock however you wish.”    
  
He crawled onto the bed, settling onto his back by the headboard, waiting for you to take the lead as he fisted his cock, stroking himself slowly as he watched you crawl towards him.   
  
“Daddy, your cock’s so big! Biggest i’ve ever seen!” You praised, filling his ego and taking him back into your hand. He hissed as you paid special attention to the sensitive, red tip, rubbing your thumb over it slowly until he started to leak.    
  
You brought your hand up to your lips to taste it, moaning in pleasure at the taste.    
“Mnnnn, I bet the whole thing tastes  _ just as good _ ,” you purred, adoring how he watched you with hungry eyes and you bent forward, running your tongue over him from base to tip.    
He moaned sinfully, deep within his chest, head tipping back into the pillows as you began to explore his cock enthusiastically with your mouth. You littered his length with soft, teasing kisses, dancing your tongue over the sensitive tip and repeatedly licking him up and down, pumping him with your hand as you did so. 

  
“Taste so good, Daddy!” You mewled, watching him with a devilish little smile as he cursed through bared teeth, loving the attention you were giving his cock.    
  
“You’re so big...I don’t think you’ll fit in my mouth...or my pussy.” 

“It will, I'll  _ make _ it fit,” he growled, lifting his hips to meet your strokes, and his words made your core clench around nothing.   
“You wanna try take it in your mouth Baby? Be a good girl for me?”   
  
You nodded eagerly, licking your lips. “I’ll try Daddy,  _ for you _ .”    
  
You wrapped your lips around his tip, already able to tell your mouth will struggle to take him, let alone your throat. Slowly you started taking him deeper, pumping him with your fist in time with your bobbing head.    
His hand grabbed the back of your head, but didn’t force you further, just holding you as he praised you for each inch you managed to swallow. Spit leaked out the corners of your mouth, down his length, helping you pump him faster.    
  
“That’s it baby, such a good girl,” he cooed. “Taking me  _ so well _ , mouth feels so good.  _ Fuck.  _ So good.”    
His other hand cupped your jaw, thumb stroking you carefully.    
“There we go, my good girl, there we go, a little further, so  _ good _ .” 

His thighs were shaking in an effort to not thrust up into your mouth, you were already struggling to take him as it is, having just over half of him in your mouth before the stretch began to become uncomfortable and having to fight your gag reflex. Your eyes were watering with the effort and with the spit leaking from your mouth you assumed you looked a complete  _ mess _ .    
  
If it weren't for the constant praise streaming from his mouth you would have felt disappointed to not be able to take all of him. But he encouraged you and eased your worries with each word that fell from his mouth.    
  


“Look at you...Fucking  _ gorgeous _ ,” he rasped, slowly rocking his hips up in experimental shallow thrusts to see how you would handle it, when you didn’t pull away he kept the slow, steady pace. “Tears running down your face, ruining that pretty mascara, covered in spit, so fucking  _ sexy _ .”   
  
You looked up at him, eyes glassy with your tears.    
  


“So fucking pretty, feel _ so good _ .” he cooed, breath catching in his throat as you swirled your tongue over his tip before swallowing him back down. “There we go, Baby,  _ ease up _ ...Daddy doesn’t want to cum just yet and i don’t think you can take me any further.”    
  
You whimpered as he gently pulled you off of him.   
“Nooo  _ Daddy, _ I can do it!” You whined, trying to go back down on him.    
  
“ _ Enough _ ,” he warned sternly. “I’m not disappointed, you’ll be able to take all of me one day, with practice, but Daddy wants us to move onto other things.” He motioned you to crawl up him further. “Come up here and sit on Daddy's face, show him just how you like your pussy to be eaten.”   
  
You flushed and did as he told, crawling up his body until you were straddling him across his torso.    
“This needs to go Baby,” he chuckled fingers sliding up your thighs and under your panties. “Take 'em off,”he ordered.    
  
You shuffled out of them, handing them over to him when he held his hand out to you.    
  
“Jeesus. You’ve soaked _ right through _ these,” he rasped hungrily, rubbing the material between his thumb and finger, entranced by the slick coating them.    
  
“My turn to taste you now Baby,” he said, tossing your underwear to the side, forearms sliding beneath your thighs, hoisting you up and onto his face.    
  
You moaned loudly as his tongue immediately started to lap at your slit, his nose bumping at your clit with each pass.    
He moaned against your core, apparently loving your taste as much as you had loved his.    
  
You felt his tongue slowly start to ease inside of you, making you moan louder. His tongue thrust in and out of you, slowly until you were trembling in his grasp. His arms locked around your thighs, keeping you still as your body began to buzz from pleasure.    
  
His tongue began to move in odd little patterns across your lips..He’s spelling his name you realized, marking his territory.    
  
“D-Daddy,” you whimpered, hips gyrating softly against his face. Rocking back and forth as he switched between spelling his name against your folds and thrusting his tongue into you.   
One of his hands moved to your ass, encouraging you to ride his face harder and faster.    
He broke away from your core to kiss up your inner thigh, “There we go baby, ride Daddy’s face, take what you need,” he panted, drunk on your taste.    
“Daddy wants to feel you cum on his face… Not taking my cock until you’re slicker than a greased up pool boy.”    
  
He went right back to your core, lapping at your clit while he shoved one, then two fingers inside of you, stretching you out.    
You rocked against his face and hand harder, hands fisting in his hair for something to grip onto as he repeatedly urged you to ride him harder and faster with a light slap to your ass.    
  
His fingers scissored inside of you, slowly stretching you wider, when he felt you could handle it, two fingers became three, stretching you as wide as your body would allow.    
When he decided you were sufficiently stretched, he went back to two fingers, only to start jack hammering them up into you at breakneck speed.    
You gasped and almost doubled over, grinding down onto his face and fingers harder, you became so blinded by pleasure you had no consideration for him to even be able to  _ breathe.  _ All you were able to do or even think about was to chase after the pleasure that was skyrocketing to its peak.    
He moaned again as you rode his face hard, taking everything you wanted from him as he found your sweet spot and started to attack you furiously there. 

  
You heard him mumble encouragements against your core, driving you closer to the edge you felt yourself hurtling towards.    
“That’s it Baby,  _ fuck, _ let go, soak Daddys face, let him  _ taste you _ .”    
  
His obscene encouragements threw you over the edge, your hips gyrating hard against his face as the air was knocked from your lungs by the strength of your orgasm, his fingers slowed down, thrusting slow and hard into you to draw it out as long as possible while his tongue flicked your clit fast. He moaned against you, his face was flooded by the liquid heat that poured out of you, he lapped it all up as if you were an oasis in the middle of a desert. 

As the intensity of it died away he gently lifted you from his face, craning his neck to place a last few kisses against your slit.   
He settled you on his torso with a proud smile on his face, looking as satisfied as you felt.    
  
“Damn, Darlin, you taste _ divine _ ,” he said proudly, wiping the slick that covered his face off with his hand and licking it up as if it was the finest meal. “I might just get addicted.” 

His hand went to your hip, thumb teasingly brushing your clit, making you whimper.    
  
“Got another one in you, Darlin? Daddy still wants you to show him how you like taking cock.”    
  
You nodded with a whine, wanting so bad to take him but feeling a little overstimulated.    
  
He reached into his bedside drawer to pull out a condom, rolling you off of him so he could roll it down, down his leaking length. 

  
With that out of the way his hands gently grasping your ass to help lift you up and over where he wanted you most. You grasped him at his base to help line him up before slowly sinking down on him, moaning at the stretch of him as you lowered yourself.    
  
He cooed at you softly the further you went, gently encouraging and praising you with sweet words as you accommodate to the stretch of him 

“There we go Darlin, look at you, taking me _ so well, _ you feel so good, so tight,  _ Fuck, _ Baby you’re  _ perfect _ .” 

  
He waited patiently for you to adjust when he could go no further, rubbing your thighs soothingly as you let the tension drift away from you.    
When you nodded, indicating you were ready he grinned at you, keeping his hands on your thighs as you placed your hands on his abdomen and slowly rocked your hips.   
His grip tightened on you, and he hissed through his teeth at the feeling, but otherwise remained still for you, allowing you take your own pleasure from him.    
  
With each gentle roll of your hips your clit grazed the dark hair at the base of his length, causing you to moan.    
  
“That feel good, Baby?” He asked, watching where the two of you met with a fiery intensity.    
You could only manage to nod and whimper in affirmation. That tight feeling in your belly slowly building back up again. 

The languid, lazy rolls of your hips sped up with each dirty phrase or question that spilled from his mouth.    
He did not once shut up but he knew exactly what to say to spur you on even further.    
“Sexiest thing I've ever seen in my life,” he drawled, voice taking on a raspy tone. “My very own private show, I am the luckiest damn man in the world.”    
  
When your speed increased from the gentle rocking to rapid humping, his praises became all the more filthier.    
  
“There we go, best _ fucking pussy _ , so  _ tight  _ and wet,” he slapped you ass, enough to sting but not enough to actually hurt you. “This hole was  _ made _ for me, huh, darlin? This pretty pussy’s  _ all mine _ right?”

You tried to block out his words as to last longer, but to no avail. You felt your arousal seep out of you, soaking him despite the fact that each word made your core clench around him.    
  
“You like that Baby? You like when Daddy talks dirty?” He grunted then chuckled when you tightened around him again. “Yeah you do, fuck, you get so  _ tight  _ when Daddy talks. Is it my voice? Or what I’m saying?”   
  
“B-both,” you stuttered out, so lost in the way he filled you up that you could barely form a cohesive response. You began desperately bouncing yourself up and down on his length, chasing your release.    
To help you along, Jack gripped your ass tightly, lifting you up and down on top of his length, his other hand furiously rubbed at your clit.    
  
“You close Baby?  _ Seems like it.” _ He paused his fingers to teasingly slap at your clit lightly, chuckling proudly when you gasped and shuddered above him. Your pace stuttering for just a moment. “The way you’re ridin’ me, so  _ needy _ , you want to cum so badly its made you all cock dumb...All you can think about is cumming huh?”    
  
You nodded, biting your lip as tears welled up in your eyes from his teasing and your desperation as you teetered on the precipice of pleasure.   
  
“Color?” he asked, pausing his taunts for just a moment.    
  
“Green.  _ Green, _ ” you whimpered as he resumed rubbing your clit with a smug grin.    
  
“Let go Baby,  _ let go _ , Daddy wants to feel just how tight you get when you cum, wants you to  _ soak _ him again.”    
  
His husky words combined with the attention he was giving your clit and the hungry glint in his eyes pushed you over your edge.    
Your walls contracted around him almost painfully, you rolled your hips into him hard to ride out your high, your perfectly manicured nails dug into his abdomen but he did not complain, he only gripped you tighter in return as he raised his own hips, forcing himself deeper to maximize your pleasure.   
  


He grunted as you milked his cock, sending him over the edge too with a flurry of curses, filling his condom.    
  
“Fuck, fuck,  _ shit.  _ Darlin, you just got so fucking  _ tight _ .” he gasped, struggling for breath as if the wind had been knocked out of him, his thighs shook in an effort to not buck into you desperately, wanting you to ride your high as long as possible. 

The two of you collapsed onto the bed at the same time, you instantly curled up on top of him, completely sated after two intense orgasms. His arms went around you, rubbing your back soothingly as you each calmed down your racing heart beats and let the sweat cool off your bodies.    
  
You were ready to fall asleep with him still inside you before he gently lifted you up and off of him, making you whine at the loss of him.    
  
“I know Baby, _ I know _ , i would love to stay inside you but Daddy needs to take care of you first,” he soothed you gently, rolling you onto your back carefully onto the other side of the bed.    
  
He stood up, taking off his condom, tying it up and throwing it into a waste paper bin by one of the doors. He strut around naked, grinning at you and giving you a playful wink when he caught you admiring the view through heavy eyes.    
  
“I’ll be right back, Baby” he promised, heading through a door you did not enter through, the bathroom, you learnt when he switched the light on.    
He came back a moment later with a warm, damp washcloth, gently washing the ruined makeup off your face before flipping it over to clean the mess you made between your legs.    
He went back to the bathroom and returned after cleaning himself up, helping you get comfy under the covers.    
  
He slid in right behind you, pulling your back flush to his front and peppering soft kisses to your shoulder, neck and face.    
  
“You did _ so well, _ Baby, Daddy’s  _ so proud _ of you,” he praised, brushing some of your hair out of your face to kiss your temple. “Such a good girl, absolutely  _ perfect _ .”    
  
You sighed contentedly, warm, satisfied and safe as he continued to praise you and kiss every inch of skin he could from his position until you fell asleep.    
The last thing you remember hearing as you drifted off was his promise to take care of you.    
  
  
  



	2. Honey Bee

**Summary for the Chapter:**

> Jack and his Baby lay out their punishment kinks just in time for Reader to get her first punishment.

**Notes for the Chapter:**

> Thank you again to @oloreaa for being my Beta reader despite not liking this Yeehonk bitch XD   
> And thanks to @talesfromtheguild for the name idea and letting me bounce ideas for this story in general off of you

Soft light filtered through sheer curtains, you stretched out lazily, feeling your joints pop and click. Idly, your foggy brain wondered just when your bed became this big and  _ soft _ . 

You fought to drift back off to sleep as memories of last night slowly came back to you,    
Cracking an eye open to confirm that  _ yes _ , you had gone home with the _ sexy  _ Daddy who wined and dined you last night. You couldn’t contain the smile on your face as you remembered everything that had happened, the slight ache between your legs reminding you of the best part.    
  
You turned over to snuggle up to your cowboy Daddy, only to find he wasn’t there. You sat up, disappointed and confused, looking around the expansive room for him, reaching to his side you deduced he had been gone only a short while by the lukewarm heat left on the sheets, you listened carefully, trying to figure out just  _ where _ he was. 

  
There was muffled shuffling outside of the room, coming from downstairs, and the delicious smell that was wafting into the room made your stomach growl.

You slid out of the covers to go explore, picking up Jack’s discarded dress shirt off the floor and throwing it on before heading off in search of him.    
  
As you left the bedroom you heard him softly humming, a familiar country tune you couldn’t quite place. Softly padding your way down the stairs there you found him, in his open kitchen, wearing a stetson, jeans and nothing else.    
  
His back was facing you, you watched the muscles there ripple as he poured batter into the waffle iron beside him, cursing when hot batter splashed back onto his bare stomach.    
  
“ _ Careful _ Daddy,” you teased, as you leaned against an island counter, making him jump slightly. 

He turned to face you with a soft smile, wiping the batter off of his front with a rag. 

“Morning  _ Honey Bee _ . Did I wake you?” he asked, rounding the island to give you a gentle kiss.

You hummed at the name, it was the same one you had used on the Sugar baby App, which you still needed to delete for him. 

“Not at all, Cowboy,” you teased, flicking his stetson playfully. 

“I was  _ hoping _ to give you breakfast in bed,” he drawled, playing with the hem of the shirt you were wearing absentmindedly. His other hand went to the small of your back, gently holding you to his front as he rocked the two of you slowly, dancing in place to music that wasn’t there. 

“Seems that plans out the window now, you hungry?” 

You nodded your head. “ _ Starving. _ I worked up  _ quite  _ an appetite last night,” you giggled, wrapping your arms around him and resting your chin on his soft front, looking up at him with a giddy smile. 

He chuckled,and bent forward to place a quick kiss to your forehead. 

“That you did, I guess riding takes a lot out of you huh?” he teased with a wink. 

You rolled your eyes at the joke, but your smile confirmed to him you liked it either way.

He was content holding you just like that, swaying gently together as if you were the only two people in existence, the only thing pulling him away from your embrace was the smell of burning batter.

“Shit, _ shit _ !” he cursed, untangling himself from your arms, trying to save what he could of the breakfast. “ _ Damn! _ ”    
  


He unplugged the iron and wafted away the faint smoke with his stetson, trying to thin it out enough to avoid the smoke alarm going off. 

“Sorry, Darlin, I was trying to be all romantic and make you breakfast,” he coughed, scraping burnt batter out of the machine. “But it seems my cooking skills ain't up to par.”    
  


“I’m just flattered that you went through the effort for  _ me _ ,” you smiled, coming up behind him and wrapping your arms around him again, kissing his bare shoulder blades. 

“Of course, gotta take care of my girl,” he moved the waffle iron to the side and cleaned up the mess on the bench.

“How bout we just order something Darl? Since i’ve made such a mess of this?” He suggested, turning in your embrace and resting his large hands on your hips. 

“Sounds  _ delightful _ ” you hummed, standing on your tiptoes to give him a chaste kiss. 

“ _ Here _ ,” he said as he pulled his phone out of his back pocket, unlocking it and passing it to you.

“You open that ‘uber’ app and pick whatever you’re fancying Princess.” 

You took the phone and browsed through the app as he cleaned up what he could, deciding on the safe bet of waffle house, since Jack had seemed so  _ insistent _ on making them for you to begin with. 

With the food ordered and on its way, you relaxed on the couch, waiting for him to finish cleaning up. You lay on your stomach, making sure his shirt was  _ only just _ covering your ass as you flipped through a TV magazine he had laying around.    
  


The rummaging in the kitchen eventually grew silent, shortly followed by warm fingers gently caressing up the back of your thigh to your ass, giving it a firm squeeze. 

You hummed, pleased as you felt his weight join you, blanketing himself over you carefully, making sure he didn’t crush you. 

You giggled as you felt his mustache tickle your neck, where he peppered many hot kisses across your skin. 

_ “D-Daddy,” _ you giggled, wiggling in his grasp as he continued to tickle you with his facial hair.

“Food will be here soon.” 

He growled, not too pleased at the idea of having to cut his playtime short before it had even had a chance to get started. 

“You’re right, Baby, we’ll have to have some fun later,” he sighed, burying his face into your neck for soft snuggles rather than the heated kisses, a change you had no complaint about either way. 

“Don’t need to get all worked up before heading to the lobby. Might give a poor delivery driver a heart attack if I answer the door full mast,” he snickered into your neck.    
  


You rolled your eyes again at his immature humour but you were once more unable to keep your own smile off of your face. 

“We can play after breakfast though.  _ Right Daddy _ ?” You asked, running your foot over this strong calves teasingly.

“Mmhhhh, of course Baby, “ he said, placing another kiss on your neck. “You only have to ask and Daddy will play with you  _ whenever _ you want. Unless you’re being a  _ brat _ for me.” 

You hummed in appreciation at the implication. 

Past Daddies had never been very...successful at the whole punishment and reward aspect of your usual relationship dynamic. Your string of bad luck when it came to your relationships didn’t just translate to the relationships with your Daddies failing, but also to how skilled they were with mixing the punishments and pleasures you hungered for.

You had never been left completely  _ satisfied  _ in a relationship before. 

But, since meeting him, there wasn't a doubt in your mind that  _ Jack’s _ ability to take care of you, to punish and pleasure you in the way you had been craving for  _ years  _ would _ finally  _ scratch that itch. To satisfy your hunger.

You weren’t _ just _ a sugar Baby for the money after all. 

“ _ I’ll be good for you _ ,” you teased, breathlessly lifting your ass up into his hips, causing him to groan. 

“Teasing's not what a  _ good girl  _ does,  _ Honey Bee _ ,” he warned, using your moniker again. It was like he was reminding you of your place, something that should have been a red flag in any other type of relationship, but with Jack, it only served to turn you on more. 

“What happened to not answering the door at full mast?” You continued to tease. 

“ _ Half mast _ ...different story,” Jack joked, snatching his phone up with one hand to check on the progress of the food. 

“It’s on its way,” he hummed, getting up off of you carefully, gently patting your ass as he straightened up. “Should  _ probably _ go put a shirt on then.” 

“Awww,” you pouted, flipping over to watch him walk over to the stairs.

“I’ll take my shirt back off when I get back with the food baby, but only if you take yours off first,  _ Honey Bee _ ,” he winked playfully at you before heading upstairs.    
  


He returned from his room, now wearing a plain white T-shirt which showed off his biceps  _ deliciously _ , and some fancy looking cowboy boots to complete his casual country look. 

“I’ll be back with the food in just a minute Darlin,” he said, coming over to you and giving you a slow, deep kiss.  _ “Be good.”  _

You batted your eyelashes up at him, playing innocent as he took off, grabbing his keys and leaving you alone in his apartment. 

Bored without his attention and curious about him, you took the opportunity alone to explore

You hopped up off the couch and started to inspect his apartment.

Upstairs you found an additional two bedrooms and bathroom , they were of little interest to you outside of their stunning views of the city, the  _ interesting _ parts of his apartment were all _ downstairs,  _ you discovered. 

A private gym, a balcony with views of central park and his own pool! You were half tempted to jump in and wait for him to return but you didn’t want to get in trouble with him, at least _ not yet.  _

You headed back inside and were about to inspect the last room of the house when you spied through the glass door a heavy wooden desk and laptop sitting on top of it, it was his office.

Remembering his warning, you loosened your grip on the handle, backing away slowly. 

“What did I tell you bout my office, Babygirl?” his deep baritone startled you, you hadn’t heard him return. 

He stood in the open lounge behind you, one hand on his hip, the other holding the takeout boxes, quirking an eyebrow at you questioningly. 

His question was a clear warning to you. 

“You said I can't go in there, and I remembered!” You explained as you turned to face him fully.

“I didn’t go in, I stopped as soon as I realized it was your office Daddy, I promise.”

He regarded you for a moment, searching your eyes.

He believed you it seemed.

“ _ Good _ ,” he purred, putting the boxes on the coffee table. He grabbed two plates and cutlery from the adjacent kitchen and returned to flop onto the couch with as much grace a man his age could muster.

“Come here Baby,” Jack beckoned you with his finger, before he sat down and toed off his boots, kicking them underneath the coffee table. 

He held out his arm in invitation of a cuddle which you happily accepted, tucking your knees under yourself as you curled up to his side. He gave you a tender kiss to your forehead then served up the food onto the plates. 

“There you go, Baby,” he smiled, handing you a plate. “Wish i could have made it myself, but this will have to do for now.  _ One day _ I'll make you a romantic breakfast in bed.” 

“I like that idea Daddy,” you hummed, digging into your food quite happily. “But i’m certainly not complaining about _ this  _ either.”    
  


You both sat, lazily cuddling as you ate your breakfast together, not in any particular rush to get on with the rest of the day. 

You finished first, putting your plate on the coffee table in front of you while you waited for him.

“You might finish it quicker if you let go of me Daddy,” you teased, causing him to cock an eyebrow at you, looking at you as if you had just grown two heads.

“Now _ why _ would I want to do that, Babygirl?” He asked, the arm around you squeezing the flesh of your exposed thigh. 

“I wasn’t  _ complaining _ Daddy, I just thought it might have been easier.”

“I know Baby,” he kissed your cheek. “But i  _ much _ prefer this.”   
  
When he had finally finished his food he stacked his plate on top of yours, picked up a blank notepad off the glass top then pulled you up onto his lap. 

“ _ Now, _ Baby,” he murmured, playing with the top button of the shirt you were wearing,  _ his _ shirt. 

“What do you say we get that little ‘contract’ sorted? Should be something we get out of the way before we have anymore  _ fun _ together, don’cha think? I don't want to overstep any boundaries with you.”    
  
You nodded in agreement, looping your arms around his neck as he began writing. 

You found it really cute the way his brow would furrow as he wrote, trying his best to balance the notepad between the two of you and not get distracted by your close proximity.    
  
When he was done, he re-read the whole page, giving it a nod of approval before flipping it for you to read. 

You made sure to read it properly, to make sure everything was covered. It was a detailed list of all the rules you had both agreed to the previous night, with the important ones underlined for emphasis,  safeword, exclusivity, communication .    
  
You smiled, giving him your approval.    
  
He then flipped to another page, writing down a list, you tried your best to read it upside down, curious as to what else he could be writing. Figuring out a few of the words you realized he was writing a list of  _ kinks.  _

He gave it another once over before showing you. 

“Like I said Princess, I don’t want to cross any boundaries with you, I need to know beforehand if you’ll be  _ just _ as enthusiastic for these as _ I am _ ,” he said, rubbing your thigh as you took the list and read it. “It's all fun and games talking punishment and rewards until I get to it and find out you don’t like what I'm doing to ya.” 

You took the pen from his hand, crossing out the hard no’s, leaving only your favorites on his expansive list.    
  


Over stimulation   
Choking   
Bondage/restraints   
Throat fucking   
Spanking   
Slapping   
Riding crop   
Public sex   
Collars   
Toys- Plugs, vibrators, Dildos- others   
Orgasm denial    
Cock warming   
Roleplay - costumes   
Rough sex   
Ice   
Candle wax

Degradation/name calling    
Fisting   
Anal   
Spitting

  
  
“Perfect” you purred, handing it back to him so he could confirm what you had approved off.    
He grinned widely as he read it, his eyes growing dark from lust. You were just the same, already feeling the familiar sensation of your arousal pooling.

“Hooo,  _ Honey Bee _ ,” he growled contentedly, reading your amendments. “You left all my _ favorites  _ on here.”    
  
He tossed the notepad onto a side table, discarding it and leaving his full attention on you.    
  
“Now keep in mind, those kinks are just for punishments and rewards...We can add more if we want to later, and we can explore other kinks any other time...I just need to know what  _ you _ want when Daddy punishes you.”    
You nodded, agreeing with his words. You were exceptionally grateful at just how serious he was taking his role and control over you, making sure you would be comfortable and feel safe with  _ everything  _ he wanted to do with you, confirming to both of you he had your  _ enthusiastic  _ consent for some of the more...extreme elements of your growing relationship. 

  
“Mind answering a question for me, Darlin?” He asked, gently undoing the top button of your shirt.

“Of course not Daddy,  _ ask away _ .”

“Got any toys at home?” His hands continued popping buttons of the shirt you were wearing, his voice was curious, with that hungry growl still hidden beneath it.

“Y-yes, i have toys,” you admitted truthfully.

“ _ Get rid of them _ ,” he ordered firmly, staring at your chest as his calloused hand slipped underneath your now unbuttoned shirt , pushing the shirt off of your shoulders, exposing you to him.

“B-but Daddy, they were _ expensive _ ,” you whined, gripping his shoulders as his large, rough hands moved to cup your breasts.

He dragged his gaze away from your tits to look you in the eyes.

“What was that? You  _ answering back _ to me _ already _ , baby?” He growled, giving your breasts a harsh squeeze in warning, making you gasp. “Your pleasure belongs to  _ me _ now, remember?  _ I _ decide when you get to feel good…And no _ toy  _ is going to do  _ my _ job _ for _ you.”

He began rolling your nipples in his fingers, causing your head to fall back in pleasure.   
He gave you a growl in warning, a wordless command of  _ eyes on me _ , and you dragged your gaze back to him, whimpering at his touches.   
You had started to get wet as you read his Kink list, just the idea of exploring them had started to work you up, but now, with his deft fingers and possessive words, you feel yourself getting wetter. 

“When you get home, you’re going to throw  _ all _ those toys you have in the trash,” he squeezed your breasts together, still toying with your nipples. “Then you’re going to send Daddy a _ photo _ to  _ prove _ it….And _ then _ , when i think you’ve _ earned  _ it, we’re going shopping for some new,  _ special  _ toys we get to use  _ together _ . For when you’ve been a  _ good girl _ for Daddy…or a _ Bad girl _ .”

You bit your lip to hide the whimper at the implications, unsuccessfully. Once again he was proving just how capable he was at his Daddy role for you.    
He chuckled at how helpless you sounded, dragging one of his hands down your front to slip between your legs, fingers quickly becoming covered in your slick.   
  
“You’re very  _ naughty _ baby, forgetting to put your panties on this morning...Only _ bad girls _ go about with no underwear,” he teased, pushing one, long finger inside you slowly.    
  
“B-But...You weren't wearing underwear last night!” You gasped, opening your legs wider to give him better access.    
  
The hand still on your tit squeezed harder. 

“Answering back _ again _ ?” he growled, shoving another finger inside of you. His other hand let go of your breast and looped around you, pulling you tight up against his front, holding you in place so he could attack your neck with his mouth. 

He kissed and licked, running his teeth over the sensitive skin there before growling right into your ear. 

“Don’t you  _ dare _ go around thinking that you can answer back to  _ me,  _ Honey Bee, or that what Daddy says  _ don’t _ matter.” 

  
Your moniker,  _ again,  _ reminding you just what you were to him, what he was to you.

One simple name you had heard many times before, but coming from his mouth,  _ his husky voice, _ it held so much power and control over you. 

The two fingers inside you pushed in as deep as they could go, curling back and forth to tease at your sweet spot. You tried to wiggle in his grasp, either to get away from the stimulation or get closer, you weren’t sure, but his grip on you held fast.

  
“If I say something makes you a  _ bad girl _ , then you best _ listen _ ...Don’t  _ matter _ if Daddy does it too, you do as I say,  _ not as I do _ ...You’re not a  _ big enough girl _ to behave like that…” he teased you, gently curling his fingers one minute then thrusting his hand into you harshly the next, fingering you as fast as he could in the position.    
“Thought you wanted to be my good girl?” he rasped, chuckling darkly when you began writhing in his hold, whining and arching your back, holding onto him for dear life, your manicured nails digging into his biceps as the obscene wet slaps of his hand thrusting into you joined your whines. 

His words and deft fingers had brought you quicker to the edge than you had ever been in your life. Something about the way he became so possessive and controlling over you turned you on so easily, you felt your core tighten up and more arousal seep down your thighs. 

Gripping his shoulders you whimpered out a warning that you were going to cum. He sped his hand up, thumb rubbing quick circles into your clit for one teasing moment, and right before you flew over the edge, he pulled his fingers free from you.    
  
“ _ W-wha _ ?” you asked befuddled, straightening back up to look at him. “Daddy  _ why _ ?” 

He stood up, tossing you onto the couch on your back before bringing his fingers to his mouth, moaning as he tasted your essence still coating them.    
  
“I’ll tell you  _ why, _ Baby,” he said, pulling his fingers free and licking his lips as if he had just eaten the _ finest _ dessert.    
“You talked back to Daddy,” he leant over top of you so his nose brushed yours. “And then I find out you’re being a _ filthy _ little girl by not wearing panties…” He slapped your thigh hard enough to sting. “And then you had the gall to talk back to me,  _ again _ .” 

He shoved his mouth against yours for a deep, domineering kiss. It was bruising. You could taste the faint flavor of the syrup from the waffles you shared, combined with your own juices, on his tongue. He cupped your jaw to deepen the kiss, then pulling away only when you had become lost to the sensation, driving you insane once again by denying you just as it got really heated.    
  
“Now, we’re both  _ new _ to this...It’s going to take a while for us  _ both  _ to learn  _ all  _ the rules,” he said, straightening up and pulling his shirt over his head, tossing it to the side, forgotten. He was back on you, kneeling between your legs before you could even admire his soft tummy again. 

“But if I let this one slide, Baby, I fear you won’t  _ learn _ the rules...If I let you get away with answering back to me, and being _ filthy _ now...Well you won’t learn your lesson,  _ will ya _ ?”   
  
One hand slid back between your legs, ghosting over your soaked folds teasingly. You whimpered again, listing your hips for more contact, batting your eyes up at him in hopes to soften him up 

  
“But since this is a  _ first  _ offence,” Jack chuckled, gently pinching your clit between two fingers, “I’ll go  _ easy _ on you. But don’t think those pretty eyes will work on me _ all _ the time, baby.” 

“ _ Daddy _ ” you whined, feeling completely helpless underneath him and loving it.    
  
“Hmmm? Now what do we think is an appropriate punishment for a first time offence?” He asked, pushing one finger back inside you, thrusting it in and out agonizingly slowly while his thumb circled your clit with feather light passes. Touching you and filling you up, but not enough to satisfy the burning need in you.    
  
He watched intently as you tried to seek out more stimulation, raising your hips up into his hand, but he put a stop to that quickly, holding your hips down with his free hand. 

“Stay still,” he growled. “You take what _ I  _ give you,  _ Honey bee _ , don’t be  _ greedy _ .” 

He watched you with his head cocked, as he decided on your punishment. 

“I think we’ll keep it  _ simple _ ,” he continued. “A spanking seems appropriate...Don’t you agree?”   
  
Jack paused, and you realized he was waiting for a response, an approval and consent over his chosen punishment. 

“Y-yes...a spanking seems fair Daddy,” you pouted, looking up at him through your lashes.    
  
“Good” he rumbled, scooping you up and gently laying you across his lap. You could feel his erection pressed up against your belly.

You wanted it inside you, but you knew you had to earn it.    
One of his arms looped around your middle, keeping you still while the other was gently massaging your ass and rubbing your pussy.    
  
_ “Listen up, _ Girl,” he said, voice firm. “You are to say “red” if this gets too much, you understand?” he asked, waiting for your verbal affirmation before continuing. “ _ Good _ , after each spank, I want you to say  _ ‘I will not talk back to Daddy’ _ . Can you repeat that for me?”   
  
“I- I will not talk back to Daddy,” you moaned, wiggling your hips to get more friction up against your pussy.    
  
“Good,” he praised again, rewarding you with more friction just where you wanted it, his palm rubbing up and down over your folds. 

“You’re going to get _ ten  _ spanks...And then Daddy's going to give you a reward afterwards,  _ if  _ you’re good for me.”    
  


You nodded, letting him know you understood.    
  
“I want you to count them out too,” was his final instruction as he raised his hand, bringing it back down against your ass with a hard SLAP!    
  
“O-one!” You yelped. “I will not talk back to Daddy!”    
  
He hummed in approval, you felt his erection brush up against your stomach again, twitching in the confines of his pants.    
  
SLAP!   
  
“Two!” I will now talk back to Daddy!” 

It continued, you tried your hardest to keep still with each slap, to stop rubbing your thighs together, but each slap only seemed to make you wetter, to make you want him more.    
  
Slap after slap after slap, you remained his good little girl.    
  
“T-Ten! I- I will not talk back to Daddy!” you cried, tears from the pain running down your face.   
  
You were left sore and sensitive, but despite the pain you felt burning pleasure fill your whole body. Jack really was living up to your dream expectations as your Daddy, you were reminded one again just how  _ perfect _ he was for you.

He proved himself more with how he treated you after a punishment. 

His hand began massaging your ass again, soothing the sting. Jack nuzzled the side of your face affectionately as he stroked the hand shaped welts forming on your ass gently. 

“Whats your color, Babygirl?” he asked softly, kissing your cheek. 

“G-green,” you panted, calming your breath and racing heart down.    
  
“Good,  _ good, _ ” he praised, carefully helping you stand on your feet, back facing him. Your legs felt like jelly, you were ready to collapse but his hands on your waist kept you standing.    
  
“You took your punishment  _ so well,  _ baby, Daddy is  _ so proud _ of you!” He kissed the growing welts, praising you. “What a  _ good girl  _ you are, taking Daddys punishment. And look at  _ this _ ,” one of his hands pushed between your legs, coating his fingers once again in your arousal. “You’re even  _ wetter _ than before...I’m not sure it's much of a punishment if you liked it that much, but a promise is a promise, you took your punishment and behaved...My little girl deserves her reward now, don’t you think?”    
  
You moaned and nodded, pushing back against his hand despite how sore you were.    
  
“Hmmmm, and I know you’re sore baby, but  _ damn _ if you didn’t make Daddy as hard as a  _ fucking rock _ through out all of that. Think you’ll be able to take my cock?” 

He chuckled when you nodded eagerly. 

“Course you can, you’re fucking  _ soaked _ .”    
  
He stood up and gently laid you down on your stomach on the couch.    
You watched over your shoulder as he pulled a condom out of his pocket and began unbuckling his belt, shoving his pants down his hips. 

Once again, he wasn’t wearing underwear, the  _ hypocrite,  _ but you held your tongue. 

Daddy had just taught you a lesson about answering back, you weren't willing to give up your reward after all that  _ delicious _ torture.    
  
“You’re ass looks fucking  _ gorgeous _ covered in my handprints,” he rasped, kicking his pants away and ripping the packet open with his teeth.

“I just want to stare at those  _ pretty _ welts as I fuck you with my cock, might get a little sore again, baby...Tell me to stop and I will.”    
  
You nodded, letting him know you understood as he positioned himself behind you, he rolled the condom on, briefly wiping up the precum that had gathered at his tip onto his hand, he held his fingers to your mouth for you to taste. 

He groaned as you swirled your tongue around them, coating his fingers in your saliva and tasting the proof of his arousal.    
  
With the condom in place, jack held himself at his base, rubbing his tip up against your soaked folds, back and forth.    
  
“Tell me you’ll be a good girl for me from now on,” he teased, you could hear that arrogant smile in his voice.    
You whined, frustrated he was holding your reward over your head so to speak.    
  
“I’ll be a good girl for you, Daddy...I won't answer back like that again!” you moaned into one of the throw pillows on the couch, holding it against your chest and face, anchoring yourself to something as you tried not to scream from frustration at his teasing.    
  
“Yeah? You’ll be a good girl and listen to Daddy too?  _ Keeping still  _ when I tell you to? Not  _ arguing _ if I deem your behaviour _ naught _ y?” 

At this point you were sure he was just trying to torture you further.    
  
“Yes! Yes Daddy! Please! I swear I'll be good, just please!” you begged. “I’ve been a good girl! Please, I just want your cock!”    
You didn’t care how pathetic or desperate you sounded as you begged him to fill you, he had manhandled you and spanked you deliciously, in a way no Daddy ever had before and if this was just a ‘mild’ punishment, it excited you further to think how he would handle something more extreme in the future. 

You had never been more aroused in your entire life. 

“ _ Good girls  _ don’t speak like that” he warned, you feared another punishment when you were this  _ close  _ to your pleasure that you actually sobbed into the pillow.    
  
“But I'll forgive you, you _ have _ been a good girl for me, taking your punishment so well....” he trailed off, distracted by the sight of his aching tip poking at your folds that were framed by his growing marks. He was so close to just...pushing in. It was agonizing having him so close to filling you up and you let him know. Pleading and sobbing harder into the pillow.

Taking mercy on you, he pushed forward _excruciatingly_ slow, making you sob in relief, satisfying your burning need, if only for a moment. 

“You’re just so  _ desperate _ for Daddy’s cock,” he rasped, enraptured by his effect on you.    
  
You moaned and continued sobbing into the pillow, overwhelmed to be finally filled with him. 

His guttural moan joined yours as he bottomed out,  _ sinfully _ loud.The stretch of his was slightly painful, given he did not take the time to prepare you as carefully as he did the night before. But the way he split you open, was _ divine.  _ He wasn’t wrong in saying you were  _ desperate _ for his cock, not when he filled you up so  _ good. _

  
“Jesus, _ fuck,  _ I don’t think I ever been inside a hole this _ wet  _ before, Baby,” he grated, rocking his hips into you slowly. 

“I can _ feel _ it, coating down our legs...Didn’t realize you were such a  _ whore  _ for punishment  _ and  _ Daddy's cock.”    
It sounded like an insult, but the wicked grin you heard in his voice told you otherwise. He was delighted at the discovery of just how needy he could make you. 

You were about to comment back when he slowly pulled out of you and then thrust back in,  _ hard _ , making you scream at the devastating pleasure of him stretching and filling you and the deliciously  _ painful _ sensation of his hips slapping up against your sore ass. 

Jack chuckled again, beginning a steady, fast and  _ deep _ pace thrusting into you. He grabbed the back of your neck, pulling you up enough so your face wasn’t buried in the throw pillow.    
  
“I want to  _ hear  _ your screams, baby,” he snarled, punctuating his sentence with a devastatingly harsh thrust. 

He laughed at you, mockingly, as you screamed again.    
  
“Fuck, I  _ love _ hearing your noises, baby, you sound so  _ hot _ , makes Daddy even  _ harder _ .” 

You felt him twitch inside you as he said it, making you whimper. 

  
You had no words left, only able to focus on the way he filled you up and rammed against your deepest spot. The burning sting of your ass each time his hips met yours drove you wild. He moaned and growled in approval at the noises you were making, but you were so lost that you weren't even aware you were making them or what you were saying. He rambled on behind you, his raspy voice praising how tight you were, how good you felt around him. You could  _ barely f _ ocus on his words.

“Rub your clit baby,” he ordered, the hand not gripping your neck rubbing your ass as he admired your marks. “Daddy wants you to cum on his cock...You’ve _ earned  _ it”    
  


You did as you were told, reaching beneath you to rub yourself with a trembling arm. You could feel his balls slap against your fingers with earth thrust. And he was right, you _ were  _ soaked, your fingers were able to glide smoothly over your bud, sending jolts of pleasure throughout your body like electricity.    
You felt your core clamping down on him instantly, making him moan.    
  
“ _ Fuck, _ just when I think you can’t get any tighter,” he rumbled. “You’re close, aren't cha Honey Bee? I can  _ feel  _ it,you’re such a little  _ cock whore _ for me, come on.. _ cum for Daddy _ , fucking _ soak _ me even more.”    
  


You whimpered, rubbing your clit faster at his words.

  
“Cum for Daddy, right _ fucking  _ now!”    
You obeyed, hit by it like a freight train. 

  
His teasing and leaving you right as you reached your peak earlier, mixed with the unbearable arousal he had caused with his spanking and dirty words resulted in the most powerful orgasm you had ever felt in your  _ entire  _ life.    
  
You felt the wind being knocked out of you as your core clamped down around him almost painfully and milk him for all he was worth. Your entire body contorted with pleasure, your legs shook violently as you tried to cling to  _ anything _ to ride out the powerful waves. 

You heard him curse behind you, slamming into you harder,  _ painfully _ so given how tender your ass was but it only added to the pleasure. 

He growled out his release, gripping your neck harder. 

“Jeesus fuck baby thats it! Yes! Yes!  _ Fuuuuck! _ ”    
His desperate bucking as he chased his own pleasure as you milked him dry simply intensified your orgasm, leaving you a breathless, panting, sweaty mess as your body shook and came down from your high. 

“ _ Perfect _ fucking pussy.”   
  
Even when you were done, as you began winding down from your high, every slight movement of him behind you made your walls flutter more, making you whimper from the over stimulation. 

He groaned deeply behind you as he pulled out, cooing gently at you as you whined.    
  
“There we go baby,  _ shhhh  _ now,” came Jack's soothing words. 

You melted into the couch, feeling like a heap of boneless jelly as your eyes started to rift close. He got up off the couch and you heard him walk to the kitchen, disposing of his condom you assumed, you were too tired to even care.    
You were surprised when he came back and rolled you over gently, picking you up bridal style.    
  
You let you a whimper of pain and confusion.    
  
“Shhh baby, Daddy’s just taking care of you,” he consoled, kissing the crown of your head. “Rest, let me do all the work.”    
  
He carried you upstairs, to his room, gently putting you back on ‘your’ side.    
  


You closed your eyes, ready to drift off as you heard him rummage about in his ensuite.    
  
He came back, and you felt him gently begin cleaning you up with another warm washcloth.    
  
“Look at my baby...so _ beautiful _ ,” he murmured tenderly, wiping up and down your thighs, throwing the wash cloth to the side to clean up later once your slick had been cleaned up. “You did  _ so well _ , took Daddys punishment and cock so well...What a _ lucky _ man I am.”    
  
He continued to praise you as he gently rolled you onto your front.   
You whimpered, your body aching and protesting but you let him manhandle you more.    
  
You heard something else rustle, then a zipper.    
There was a pop of a cap followed by the soothing sensation of his hands rubbing cream into your abused skin.    
You whined, the cream too cold for your burning skin but he soothed you with gentle kisses peppered along your shoulder blades.    
“Let Daddy take care of you, it will be done soon,” he promised. With your welts thoroughly coated you sighed in content, already feeling the stinging sensation start to fade away.    
  
“There we go,” he praised, packing up what you now knew to be the first aid kit. He went to put it away and wash his hands before he returned. He moved to lay next to you, fidgeting a bit, wanting to pull you up against him but not willing to agitate your sore ass. He contented himself by laying on his side, watching you as one hand resting on your back, stroking it affectionately and limbs intertwined with yours.    
  
He kissed everywhere he could reach, just as he had last night, he spoke to you gently, letting you focus on his words rather than on how sore you were.    
“Rest Baby, when you wake up, we’ll have a lot of work to do,” he hummed. “Gonna get'cha all cleaned up, put a nice meal in your belly, make sure you’re all taken care of.”    
  
You snuggled deeper into the plush pillow you were laying on, a smile forming on your lips at his soft promises.    
  
“Then Daddy's going to have to get ya home, gonna need to get your allowance sorted, and see you get your appointment for your implant...Daddy wants you without a condom as soon as possible.” he teased, his fingers dancing on your back gently, making the flesh jump.    
  


You whined at the ticklish sensation and he chuckled.    
  
“Go to sleep baby, i’ll be here when you wake up this time,” he murmured the promise into your ear as you finally drifted off.    
  


  
  



End file.
